Long-term field measured yield data provides good opportunity to assess the impacts of climate and management on crop production. This study used the yield results from a long-term field experiment (1979–2012) at Luancheng Experimental Station in the central part of the North China Plain (NCP) to analyze the seasonal yield variation of winter wheat (Triticum aestivum L.) under the condition of sufficient water supply. The yield change of winter wheat over the last 33 growing seasons was divided into three time periods: the 1980s, the 1990s, and the years of 2001–2012. The grain yield of winter wheat during the 1980s was relative stable. During the 1990s, the annual yield of this crop was continuously increased by 193 kg/ha/year (P < 0.01). While for the past 12 years, yield of winter wheat was maintained at relative higher level, but with larger seasonal yield variation than that back in 1980s. CERES-Wheat model was calibrated and was used to verify the effects of management practices on grain yield. Seven scenarios were simulated with and without improvements in management. The simulated results show that the yield of winter wheat was decreased by 5.3% during 1990s and by 9.2% during the recent 12 seasons, compared with that during 1980s, under the scenario that the yield of winter wheat was solely affected by weather. Seasonal yield variation caused by weather factors was around −39% to 20%, indicating the great effects of weather on yearly yield variation. Yield improvement by cultivars was around 24.7% during 1990s and 52.0% during the recent 12 seasons compared with that during 1980s. The yield improvement by the increase in soil fertility and chemical fertilizer input was 7.4% and 6.8% during the two periods, respectively. The initial higher soil fertility and chemical fertilizer input might be the reasons that the responses of crop production to the further increase in chemical fertilizer were small during the simulation period. Correlation analysis of the grain yield from the field measured data with weather factors showed that sunshine hours and diurnal temperature difference (DTR) were positively, and relative humidity was negatively related to grain yield of winter wheat. The climatic change trends in this area showed that the DTR and sunshine hours were declining. This type of climatic change trend might further negatively affect winter wheat production in the future.